甲基3-甲酰基-1-甲基-1H-吲哚-4-羧酸酯 | 65923-20-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 甲基3-甲酰基-1-甲基-1H-吲哚-4-羧酸酯
• 英文名称: 3-formyl-1-methyl-1H-indole-4-carboxylic acid methyl ester
• 英文别名: 4-Carbomethoxy-1-methyl-indol-3-carboxaldehyd；3-formyl-1-methyl-indole-4-carboxylic acid methyl ester；methyl 1-methyl-3-formylindole-4-carboxylate；methyl 3-formyl-1-methyl-1H-indole-4-carboxylate；methyl 3-formyl-1-methylindole-4-carboxylate
• CAS: 65923-20-8
• 化学式: C₁₂H₁₁NO₃
• mdl: MFCD09864027
• 分子量: 217.224
• InChiKey: AICKYZOVKLTAFW-UHFFFAOYSA-N

物化性质

• 熔点：
  130 °C
• 沸点：
  388.5±22.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  48.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲基3-甲酰基-1-甲基-1H-吲哚-4-羧酸酯 在 二氯乙酸 、 sodium tetrahydroborate 、 正丁基锂 、 草酰氯 、 palladium on activated charcoal 、 水 、 氢气 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 12.5h， 生成
  参考文献：
  名称：

  一种氮杂环二酮化合物及其制备方法

  摘要：

  本发明提供了一种氮杂环二酮化合物，其特征在于，为如下结构所示的化合物：该化合物对帽依赖性核酸内切酶抑有制活性。

  公开号：

  CN111606928A
• 作为产物：
  描述：

  吲哚-4-羧酸甲酯 在 sodium hydride 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 甲基3-甲酰基-1-甲基-1H-吲哚-4-羧酸酯
  参考文献：
  名称：

  一种氮杂环二酮化合物及其制备方法

  摘要：

  本发明提供了一种氮杂环二酮化合物，其特征在于，为如下结构所示的化合物：该化合物对帽依赖性核酸内切酶抑有制活性。

  公开号：

  CN111606928A

文献信息

• 5-HT3 RECEPTOR MODULATORS, METHODS OF MAKING, AND USE THEREOF
  申请人：Manning David D.

  公开号：US20090298809A1

  公开（公告）日：2009-12-03

  Novel 5-HT 3 receptor modulators are disclosed. These compounds are used in the treatment of various disorders, including chemotherapy-induced nausea and vomiting, post-operative nausea and vomiting, and irritable bowel syndrome. Methods of making these compounds are also described in the present invention.

  揭示了新型5-HT3受体调节剂。这些化合物用于治疗各种疾病，包括化疗诱发的恶心和呕吐、术后恶心和呕吐以及肠易激综合征。本发明还描述了制备这些化合物的方法。
• Synthesis and anticancer activity evaluation of 3-(4-oxo-2-thioxothiazolidin-5-yl)-1<i>H</i>-indole-carboxylic acids derivatives
  作者：Anna Kryshchyshyn-Dylevych、Myroslav Garazd、Andrew Karkhut、Sviatoslav Polovkovych、Roman Lesyk

  DOI：10.1080/00397911.2020.1786124

  日期：2020.9.16

  1-oxo-9H-thiopyrano[3,4-b]indole-3-carboxylic acids and dimerized 3-(4-carboxy-1H-3-indolyl)-2-propenoic acids via alkaline hydrolysis of 3-(rhodanin-5-yl)-1H-indole-2-carboxylic acids derivatives was elaborated. Anticancer activity screening in NCI60-cell lines assay allowed identification of 5-fluoro-3-(4-oxo-2-thioxothiazolidin-5-ylidenemethyl)-1H-indole-2-carboxylic acid methyl ester 2a with significant antimitotic

  摘要 一种温和高效的合成 1-oxo-9H-thiopyrano[3,4-b]indole-3- 羧酸和二聚 3-(4-carboxy-1H-3-indoyl)-2-propenoic 酸的方法通过碱性水解 3-(rhodanin-5-yl)-1H-indole-2- 羧酸衍生物进行了详细说明。NCI60 细胞系测定中的抗癌活性筛选允许鉴定具有显着抗有丝分裂活性的 5-fluoro-3-(4-oxo-2-thioxothiazolidin-5-ylidenemethyl)-1H-indole-2-羧酸甲酯 2a，在微摩尔和亚微摩尔浓度。图形概要
• 6-oxoazepinoindole compounds, and pharmaceutical compositions containing
  申请人：Kali-Chemie Pharma GmbH

  公开号：US05272143A1

  公开（公告）日：1993-12-21

  Pharmacologically active compounds corresponding to the general formula I ##STR1## in which R.sup.1 represents hydrogen, a lower alkyl or cycloalkyl-alkyl group or an optionally substituted phenyl-lower alkyl group, R.sup.2 denotes hydrogen or a lower alkyl group optionally substituted in the .alpha.-position to the nitrogen atom by lower alkoxy, R.sup.3 denotes hydrogen, lower alkyl, lower alkoxy, halogen or hydroxyl, n represents 1 or, if the --(CH.sub.2).sub.n -- chain is in the 4-position of the ring structure, also represents 2, R.sup.4 denotes hydrogen, lower alkyl, cycloalkyl, cycloalkyl-lower alkyl or an optionally substituted phenyl-lower alkyl group, and R.sup.5 denotes hydrogen, lower alkyl, cycloalkyl, cycloalkyl-lower alkyl or an optionally substituted phenyl-lower alkyl group, or R.sup.4 and R.sup.5, together with the nitrogen atom to which they are bonded, form a heterocycle and D represents a bond, or, if R.sup.4 and R.sup.5 do not denote hydrogen, also represents the --N.dbd.CH-- group, and their physiologically acceptable acid addition salts are described, and also processes and intermediates for their preparation.

  一般式I对应的药理活性化合物如下：##STR1## 其中，R.sup.1代表氢、较低的烷基或环烷基-烷基基团或可选择性取代的苯基-较低的烷基基团，R.sup.2代表氢或可选择性取代于氮原子的α-位置的较低烷氧基的较低烷基基团，R.sup.3代表氢、较低的烷基、较低烷氧基、卤素或羟基，n代表1或，如果-(CH.sub.2).sub.n-链在环结构的4位，则也代表2，R.sup.4代表氢、较低的烷基、环烷基、环烷基-较低的烷基或可选择性取代的苯基-较低的烷基基团，R.sup.5代表氢、较低的烷基、环烷基、环烷基-较低的烷基或可选择性取代的苯基-较低的烷基基团，或R.sup.4和R.sup.5与它们连接的氮原子一起形成杂环，D代表键，或者如果R.sup.4和R.sup.5不代表氢，则还代表-N.dbd.CH-基团。此外，还描述了它们的生理上可接受的酸加成盐，以及制备它们的过程和中间体。
• Electrosynthesis of (hetero)aryl nitriles from α-imino-oxy acids <i>via</i> oxidative decarboxylation/N–O cleavage
  作者：Hui-Shan Lin、Shu-Jun Chen、Jing-Mei Huang

  DOI：10.1039/d2cc02986c

  日期：——

  A new method for the synthesis of (hetero)aryl nitriles via iminyl radicals has been developed through the electrochemical oxidative decarboxylation of α-imino-oxy acids. This protocol provides an efficient approach to nitriles with a broad range of functional-group tolerance under ambient conditions and can be applied for one-pot gram-scale synthesis.

  通过 α-亚氨基-含氧酸的电化学氧化脱羧，开发了一种通过亚氨基自由基合成（杂）芳基腈的新方法。该协议为在环境条件下具有广泛的官能团耐受性的腈提供了一种有效的方法，可用于一锅克级合成。
• 1,2,3-Thiadiazole substituted pyrazolones as potent KDR/VEGFR-2 kinase inhibitors
  作者：Rabindranath Tripathy、Arup Ghose、Jasbir Singh、Edward R. Bacon、Thelma S. Angeles、Shi X. Yang、Mark S. Albom、Lisa D. Aimone、Joseph L. Herman、John P. Mallamo

  DOI：10.1016/j.bmcl.2006.12.054

  日期：2007.3

  KDR kinase inhibition is considered to play an important role in regulating angiogenesis, which is vital for the survival and proliferation of tumor cells. Recently we disclosed a structure-based kinase inhibitor design strategy which led to the identification of a new class of VEGFR-2/KDR kinase inhibitors bearing heterocyclic substituted pyrazolones as the core template. Instability in a rat S9 preparation and poor iv PK profiles for most of these inhibitors necessitated exploration of new pyrazolones to identify new analogs with improved metabolic stability. Optimization of the heterocyclic moiety led to the identification of the thiadiazole series of pyrazolones (D) as potent VEGFR-2/KDR kinase inhibitors. SAR modifications, kinase selectivity profiling, and structural elements for improved PK properties were explored. Oral bioavailability up to 29% was achieved in the rat. Modeling results based on the Glide XP docking approach supported our postulation regarding the interaction of the lactam segment of the pyrazolones with the hinge region of the KDR kinase. (c) 2007 Elsevier Ltd. All rights reserved.